NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.16
Volume:	289.924
LogP:	3.799
LogD:	3.198
LogS:	-2.969
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	3.325
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.624
MDCK Permeability:	1.778806654328946e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	96.81159210205078%
Volume Distribution (VD):	2.588
Pgp-substrate:	3.6660890579223633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.766
CYP1A2-substrate:	0.316
CYP2C19-inhibitor:	0.398
CYP2C19-substrate:	0.223
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.676
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.76
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	17.5
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.761
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.863
Carcinogencity:	0.299
Eye Corrosion:	0.021
Eye Irritation:	0.945
Respiratory Toxicity:	0.253

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC475078

Natural Product ID:	NPC475078
*Common Name:**	2-[(1Z)-3-Hydroxy-3,7-Dimethylocta-1,6-Dienyl]Benzene-1,4-Diol
IUPAC Name:	2-[(1Z)-3-hydroxy-3,7-dimethylocta-1,6-dienyl]benzene-1,4-diol
Synonyms:
Standard InCHIKey:	LYEFFNNYUIQXHS-NTMALXAHSA-N
Standard InCHI:	InChI=1S/C16H22O3/c1-12(2)5-4-9-16(3,19)10-8-13-11-14(17)6-7-15(13)18/h5-8,10-11,17-19H,4,9H2,1-3H3/b10-8-
SMILES:	CC(=CCCC(/C=Cc1cc(O)ccc1O)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495869
PubChem CID:	9992880
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5373	Cordia alliodora	Species	Cordiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10757739]
NPO5373	Cordia alliodora	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1
Others	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	Activity	=	5.0	ug	PMID[460806]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	MIC	=	15.0	ug.mL-1	PMID[460806]
NPT20	Organism	Candida albicans	Candida albicans	Activity	>	50.0	ug	PMID[460806]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	>	50.0	ug ml-1	PMID[460806]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC475078 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	1900
0.2-0.3	6233
0.3-0.4	13321
0.4-0.5	5980
0.5-0.6	10028
0.6-0.7	3825
0.7-0.8	896
0.8-0.85	182
0.85-0.9	75
0.9-0.95	14
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC152097
0.9681	High Similarity	NPC80800
0.9677	High Similarity	NPC260775
0.9579	High Similarity	NPC108497
0.9574	High Similarity	NPC248396
0.9574	High Similarity	NPC130756
0.9574	High Similarity	NPC12931
0.9574	High Similarity	NPC70677
0.9574	High Similarity	NPC48730
0.9574	High Similarity	NPC129373
0.956	High Similarity	NPC29373
0.9286	High Similarity	NPC53740
0.9271	High Similarity	NPC477685
0.9192	High Similarity	NPC474352
0.9184	High Similarity	NPC47284
0.9091	High Similarity	NPC155072
0.9091	High Similarity	NPC469913
0.9032	High Similarity	NPC231150
0.9	High Similarity	NPC320439
0.898	High Similarity	NPC269212
0.8969	High Similarity	NPC72729
0.8969	High Similarity	NPC130103
0.8958	High Similarity	NPC88420
0.8936	High Similarity	NPC147284
0.8936	High Similarity	NPC3358
0.8936	High Similarity	NPC162314
0.8936	High Similarity	NPC306884
0.8936	High Similarity	NPC210497
0.8936	High Similarity	NPC94139
0.8925	High Similarity	NPC192
0.8922	High Similarity	NPC471535
0.8913	High Similarity	NPC27974
0.8889	High Similarity	NPC130817
0.8889	High Similarity	NPC475580
0.8878	High Similarity	NPC12221
0.8842	High Similarity	NPC245187
0.8835	High Similarity	NPC54373
0.8824	High Similarity	NPC473524
0.8824	High Similarity	NPC98392
0.8812	High Similarity	NPC233320
0.8804	High Similarity	NPC407
0.8804	High Similarity	NPC307235
0.8791	High Similarity	NPC150837
0.8791	High Similarity	NPC286904
0.8788	High Similarity	NPC471228
0.8788	High Similarity	NPC233827
0.8788	High Similarity	NPC235762
0.8776	High Similarity	NPC174911
0.8763	High Similarity	NPC79241
0.8763	High Similarity	NPC6597
0.8763	High Similarity	NPC474073
0.875	High Similarity	NPC474920
0.8725	High Similarity	NPC279887
0.8725	High Similarity	NPC68260
0.8723	High Similarity	NPC312304
0.87	High Similarity	NPC272029
0.87	High Similarity	NPC475225
0.87	High Similarity	NPC93831
0.8696	High Similarity	NPC155393
0.8687	High Similarity	NPC252105
0.8673	High Similarity	NPC299762
0.8673	High Similarity	NPC33675
0.866	High Similarity	NPC312132
0.866	High Similarity	NPC259512
0.8654	High Similarity	NPC266937
0.8654	High Similarity	NPC470770
0.8654	High Similarity	NPC77772
0.8654	High Similarity	NPC228609
0.8654	High Similarity	NPC469912
0.8646	High Similarity	NPC76938
0.8646	High Similarity	NPC152415
0.8641	High Similarity	NPC26013
0.8641	High Similarity	NPC282855
0.8632	High Similarity	NPC270547
0.8627	High Similarity	NPC66834
0.8617	High Similarity	NPC177420
0.8617	High Similarity	NPC280347
0.8586	High Similarity	NPC166761
0.8571	High Similarity	NPC177962
0.8571	High Similarity	NPC302371
0.8571	High Similarity	NPC62867
0.8558	High Similarity	NPC208229
0.8557	High Similarity	NPC32714
0.8542	High Similarity	NPC55903
0.8529	High Similarity	NPC310456
0.8529	High Similarity	NPC54765
0.8529	High Similarity	NPC67250
0.8526	High Similarity	NPC55561
0.8511	High Similarity	NPC25493
0.8511	High Similarity	NPC113460
0.8511	High Similarity	NPC19680
0.8505	High Similarity	NPC473718
0.8476	Intermediate Similarity	NPC275627
0.8447	Intermediate Similarity	NPC158253
0.8447	Intermediate Similarity	NPC204901
0.8447	Intermediate Similarity	NPC232523
0.8438	Intermediate Similarity	NPC306074
0.8438	Intermediate Similarity	NPC204210
0.8431	Intermediate Similarity	NPC37802
0.8431	Intermediate Similarity	NPC138942
0.8426	Intermediate Similarity	NPC141001
0.8421	Intermediate Similarity	NPC123273
0.8421	Intermediate Similarity	NPC242240
0.8421	Intermediate Similarity	NPC98772
0.8421	Intermediate Similarity	NPC318325
0.8416	Intermediate Similarity	NPC24404
0.8416	Intermediate Similarity	NPC196479
0.8416	Intermediate Similarity	NPC313030
0.8416	Intermediate Similarity	NPC106396
0.8416	Intermediate Similarity	NPC71002
0.8416	Intermediate Similarity	NPC242342
0.8416	Intermediate Similarity	NPC302219
0.8416	Intermediate Similarity	NPC222522
0.8416	Intermediate Similarity	NPC146798
0.8416	Intermediate Similarity	NPC85479
0.8416	Intermediate Similarity	NPC53051
0.8416	Intermediate Similarity	NPC249828
0.8416	Intermediate Similarity	NPC94351
0.8416	Intermediate Similarity	NPC168303
0.8411	Intermediate Similarity	NPC197513
0.8411	Intermediate Similarity	NPC471534
0.8404	Intermediate Similarity	NPC23167
0.8404	Intermediate Similarity	NPC184169
0.84	Intermediate Similarity	NPC10588
0.84	Intermediate Similarity	NPC294741
0.84	Intermediate Similarity	NPC225506
0.8396	Intermediate Similarity	NPC228452
0.8387	Intermediate Similarity	NPC248817
0.8384	Intermediate Similarity	NPC77492
0.8384	Intermediate Similarity	NPC156313
0.8367	Intermediate Similarity	NPC274678
0.8367	Intermediate Similarity	NPC26244
0.8367	Intermediate Similarity	NPC222146
0.8365	Intermediate Similarity	NPC241549
0.8365	Intermediate Similarity	NPC169450
0.8365	Intermediate Similarity	NPC95344
0.8365	Intermediate Similarity	NPC306295
0.835	Intermediate Similarity	NPC12640
0.835	Intermediate Similarity	NPC99836
0.835	Intermediate Similarity	NPC201662
0.8349	Intermediate Similarity	NPC320864
0.8333	Intermediate Similarity	NPC47950
0.8333	Intermediate Similarity	NPC323810
0.8333	Intermediate Similarity	NPC244513
0.8333	Intermediate Similarity	NPC288411
0.8333	Intermediate Similarity	NPC218879
0.8333	Intermediate Similarity	NPC227458
0.8318	Intermediate Similarity	NPC28784
0.8318	Intermediate Similarity	NPC76400
0.8318	Intermediate Similarity	NPC296144
0.8317	Intermediate Similarity	NPC192032
0.8317	Intermediate Similarity	NPC137415
0.8317	Intermediate Similarity	NPC72947
0.8317	Intermediate Similarity	NPC166313
0.8317	Intermediate Similarity	NPC284011
0.8317	Intermediate Similarity	NPC147310
0.8317	Intermediate Similarity	NPC294186
0.8317	Intermediate Similarity	NPC24407
0.8317	Intermediate Similarity	NPC11280
0.83	Intermediate Similarity	NPC252821
0.83	Intermediate Similarity	NPC128723
0.83	Intermediate Similarity	NPC122005
0.8298	Intermediate Similarity	NPC197783
0.8286	Intermediate Similarity	NPC33728
0.8286	Intermediate Similarity	NPC316052
0.8286	Intermediate Similarity	NPC19808
0.8283	Intermediate Similarity	NPC473388
0.828	Intermediate Similarity	NPC124436
0.828	Intermediate Similarity	NPC265146
0.8273	Intermediate Similarity	NPC206205
0.8265	Intermediate Similarity	NPC316301
0.8265	Intermediate Similarity	NPC151715
0.8265	Intermediate Similarity	NPC128062
0.8265	Intermediate Similarity	NPC289769
0.8265	Intermediate Similarity	NPC27323
0.8257	Intermediate Similarity	NPC69539
0.8252	Intermediate Similarity	NPC471350
0.8252	Intermediate Similarity	NPC117115
0.8247	Intermediate Similarity	NPC304541
0.8241	Intermediate Similarity	NPC114918
0.8241	Intermediate Similarity	NPC473931
0.8241	Intermediate Similarity	NPC474050
0.8241	Intermediate Similarity	NPC474114
0.8235	Intermediate Similarity	NPC168393
0.8235	Intermediate Similarity	NPC168829
0.8229	Intermediate Similarity	NPC258219
0.8229	Intermediate Similarity	NPC70436
0.8224	Intermediate Similarity	NPC98372
0.8208	Intermediate Similarity	NPC132720
0.82	Intermediate Similarity	NPC109955
0.8198	Intermediate Similarity	NPC471449
0.8198	Intermediate Similarity	NPC51341
0.8191	Intermediate Similarity	NPC175313
0.819	Intermediate Similarity	NPC174981
0.8182	Intermediate Similarity	NPC246679
0.8182	Intermediate Similarity	NPC269414
0.8182	Intermediate Similarity	NPC257182
0.8182	Intermediate Similarity	NPC238176
0.8182	Intermediate Similarity	NPC8392
0.8182	Intermediate Similarity	NPC187993

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC475078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	1090
0.2-0.3	1511
0.3-0.4	3006
0.4-0.5	1811
0.5-0.6	1081
0.6-0.7	346
0.7-0.8	56
0.8-0.85	12
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD289	Clinical (unspecified phase)
0.8947	High Similarity	NPD844	Approved
0.866	High Similarity	NPD288	Approved
0.8505	High Similarity	NPD6671	Approved
0.8454	Intermediate Similarity	NPD2934	Approved
0.8454	Intermediate Similarity	NPD2933	Approved
0.8396	Intermediate Similarity	NPD7635	Approved
0.8367	Intermediate Similarity	NPD2859	Approved
0.8367	Intermediate Similarity	NPD2860	Approved
0.8351	Intermediate Similarity	NPD845	Approved
0.83	Intermediate Similarity	NPD3020	Approved
0.828	Intermediate Similarity	NPD111	Approved
0.8265	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD846	Approved
0.8137	Intermediate Similarity	NPD940	Approved
0.8113	Intermediate Similarity	NPD4750	Phase 3
0.8	Intermediate Similarity	NPD1809	Phase 2
0.7944	Intermediate Similarity	NPD3021	Approved
0.7944	Intermediate Similarity	NPD3022	Approved
0.7912	Intermediate Similarity	NPD9088	Approved
0.7864	Intermediate Similarity	NPD1242	Phase 1
0.783	Intermediate Similarity	NPD1445	Approved
0.783	Intermediate Similarity	NPD1444	Approved
0.7757	Intermediate Similarity	NPD2342	Discontinued
0.767	Intermediate Similarity	NPD9273	Approved
0.7664	Intermediate Similarity	NPD968	Approved
0.7615	Intermediate Similarity	NPD1792	Phase 2
0.7586	Intermediate Similarity	NPD3496	Discontinued
0.7547	Intermediate Similarity	NPD9500	Approved
0.75	Intermediate Similarity	NPD2229	Approved
0.75	Intermediate Similarity	NPD2228	Approved
0.75	Intermediate Similarity	NPD2234	Approved
0.7479	Intermediate Similarity	NPD6696	Suspended
0.7478	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD228	Approved
0.7473	Intermediate Similarity	NPD9087	Approved
0.7434	Intermediate Similarity	NPD9618	Approved
0.7434	Intermediate Similarity	NPD9614	Approved
0.7434	Intermediate Similarity	NPD497	Approved
0.74	Intermediate Similarity	NPD9295	Approved
0.7358	Intermediate Similarity	NPD3028	Approved
0.735	Intermediate Similarity	NPD4059	Approved
0.7345	Intermediate Similarity	NPD1398	Phase 1
0.7345	Intermediate Similarity	NPD496	Approved
0.7345	Intermediate Similarity	NPD498	Approved
0.7345	Intermediate Similarity	NPD495	Approved
0.7328	Intermediate Similarity	NPD3091	Approved
0.7321	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD9608	Approved
0.7315	Intermediate Similarity	NPD9610	Approved
0.7311	Intermediate Similarity	NPD2233	Approved
0.7311	Intermediate Similarity	NPD2230	Approved
0.7311	Intermediate Similarity	NPD2232	Approved
0.7304	Intermediate Similarity	NPD7340	Approved
0.7295	Intermediate Similarity	NPD2861	Phase 2
0.7281	Intermediate Similarity	NPD1791	Approved
0.7281	Intermediate Similarity	NPD1793	Approved
0.7273	Intermediate Similarity	NPD290	Approved
0.7257	Intermediate Similarity	NPD9379	Approved
0.7257	Intermediate Similarity	NPD9377	Approved
0.725	Intermediate Similarity	NPD4749	Approved
0.725	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9616	Approved
0.7241	Intermediate Similarity	NPD9615	Approved
0.7241	Intermediate Similarity	NPD9613	Approved
0.7234	Intermediate Similarity	NPD9294	Approved
0.7232	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2932	Approved
0.7203	Intermediate Similarity	NPD4626	Approved
0.7203	Intermediate Similarity	NPD3019	Approved
0.7193	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD316	Approved
0.7155	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1983	Approved
0.7143	Intermediate Similarity	NPD1981	Approved
0.7143	Intermediate Similarity	NPD1980	Approved
0.7119	Intermediate Similarity	NPD4093	Discontinued
0.7097	Intermediate Similarity	NPD600	Approved
0.7097	Intermediate Similarity	NPD596	Approved
0.7083	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3092	Approved
0.7083	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD709	Approved
0.7059	Intermediate Similarity	NPD1778	Approved
0.7059	Intermediate Similarity	NPD4589	Approved
0.7054	Intermediate Similarity	NPD9266	Approved
0.7054	Intermediate Similarity	NPD74	Approved
0.7054	Intermediate Similarity	NPD2684	Approved
0.7041	Intermediate Similarity	NPD9089	Approved
0.704	Intermediate Similarity	NPD4625	Phase 3
0.7034	Intermediate Similarity	NPD5303	Approved
0.7034	Intermediate Similarity	NPD5304	Approved
0.7009	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9493	Approved
0.6992	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3094	Phase 2
0.6991	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD9267	Approved
0.6964	Remote Similarity	NPD9263	Approved
0.6964	Remote Similarity	NPD9264	Approved
0.6942	Remote Similarity	NPD1201	Approved
0.6939	Remote Similarity	NPD9093	Approved
0.6929	Remote Similarity	NPD839	Approved
0.6929	Remote Similarity	NPD840	Approved
0.6917	Remote Similarity	NPD3095	Discontinued
0.6917	Remote Similarity	NPD9384	Approved
0.6917	Remote Similarity	NPD1751	Approved
0.6917	Remote Similarity	NPD2286	Discontinued
0.6917	Remote Similarity	NPD9381	Approved
0.6897	Remote Similarity	NPD5283	Phase 1
0.6891	Remote Similarity	NPD1759	Phase 1
0.6891	Remote Similarity	NPD7330	Discontinued
0.6885	Remote Similarity	NPD2235	Phase 2
0.6885	Remote Similarity	NPD2231	Phase 2
0.687	Remote Similarity	NPD2935	Discontinued
0.6855	Remote Similarity	NPD3055	Approved
0.6855	Remote Similarity	NPD3053	Approved
0.685	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD9244	Approved
0.6833	Remote Similarity	NPD5691	Approved
0.6833	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1357	Approved
0.6833	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1755	Approved
0.6829	Remote Similarity	NPD9622	Approved
0.6814	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.681	Remote Similarity	NPD821	Approved
0.681	Remote Similarity	NPD7843	Approved
0.6807	Remote Similarity	NPD16	Approved
0.6807	Remote Similarity	NPD1758	Phase 1
0.6807	Remote Similarity	NPD856	Approved
0.6803	Remote Similarity	NPD1611	Approved
0.68	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6584	Phase 3
0.678	Remote Similarity	NPD255	Approved
0.678	Remote Similarity	NPD256	Approved
0.678	Remote Similarity	NPD7157	Approved
0.6777	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2667	Approved
0.6777	Remote Similarity	NPD2668	Approved
0.6774	Remote Similarity	NPD5311	Approved
0.6774	Remote Similarity	NPD5310	Approved
0.6772	Remote Similarity	NPD3027	Phase 3
0.675	Remote Similarity	NPD1548	Phase 1
0.6746	Remote Similarity	NPD5736	Approved
0.6744	Remote Similarity	NPD4060	Phase 1
0.6744	Remote Similarity	NPD2238	Phase 2
0.6726	Remote Similarity	NPD3134	Approved
0.6723	Remote Similarity	NPD7636	Approved
0.6721	Remote Similarity	NPD3143	Discontinued
0.672	Remote Similarity	NPD1470	Approved
0.6696	Remote Similarity	NPD5451	Approved
0.6695	Remote Similarity	NPD475	Phase 2
0.6694	Remote Similarity	NPD5585	Approved
0.6693	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD4624	Approved
0.6667	Remote Similarity	NPD9621	Approved
0.6667	Remote Similarity	NPD858	Approved
0.6667	Remote Similarity	NPD318	Approved
0.6667	Remote Similarity	NPD4817	Approved
0.6667	Remote Similarity	NPD9620	Approved
0.6667	Remote Similarity	NPD1138	Approved
0.6667	Remote Similarity	NPD317	Approved
0.6667	Remote Similarity	NPD4818	Approved
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD2195	Approved
0.6667	Remote Similarity	NPD9073	Approved
0.6667	Remote Similarity	NPD2194	Approved
0.6667	Remote Similarity	NPD859	Approved
0.6667	Remote Similarity	NPD602	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD1091	Approved
0.6667	Remote Similarity	NPD9619	Approved
0.6667	Remote Similarity	NPD599	Approved
0.6667	Remote Similarity	NPD1535	Discovery
0.664	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD9697	Approved
0.6635	Remote Similarity	NPD9094	Approved
0.6614	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3636	Approved
0.6614	Remote Similarity	NPD2237	Approved
0.6614	Remote Similarity	NPD3637	Approved
0.6614	Remote Similarity	NPD3635	Approved
0.6614	Remote Similarity	NPD1712	Approved
0.6613	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3070	Discontinued
0.6613	Remote Similarity	NPD1481	Phase 2
0.6613	Remote Similarity	NPD2561	Approved
0.6613	Remote Similarity	NPD2562	Approved
0.6612	Remote Similarity	NPD9545	Approved
0.6607	Remote Similarity	NPD9261	Approved
0.6607	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD601	Approved
0.6589	Remote Similarity	NPD597	Approved
0.6589	Remote Similarity	NPD598	Approved
0.6587	Remote Similarity	NPD1135	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data